Chief of Staff
Employment Information
Job Description
Chief of Staff managing strategic initiatives at cybersecurity firm Trail of Bits. Responsible for CEO workflow, accountability, and cross-departmental strategic planning.
Responsibilities:
- Manage the CEO's day-to-day workflow and act as a thought partner on company strategy, ensuring focus on the right priorities to achieve organizational goals.
- Build and maintain accountability systems that track commitments across the organization so that when the CEO asks for something important, it gets captured, scheduled, and completed on a predictable timeline.
- Conduct after-action reviews following critical incidents (customer escalations, PR issues, operational failures), gathering context from multiple sources and proposing documented process improvements.
- Draft reports, speeches, and presentations on behalf of the CEO; prepare the CEO for meetings by researching and creating materials that facilitate productive engagement.
- Lead annual strategic planning, oversee cross-departmental projects, and coordinate key stakeholders to drive progress and decision-making on the company's most complex challenges.
- Take ownership of difficult conversations about performance and expectations, communicating firmly and clearly across the organization while building trust and maintaining collaborative relationships.
- Coordinate training sessions on new processes, propose systems to streamline operations, and identify metrics that matter for tracking business performance.
Requirements:
- 8+ years in consulting, program management, or operational roles in tech companies, with a track record of helping executives and teams hit ambitious goals.
- Exceptional at writing and presenting to senior audiences, with experience giving board-level presentations and drafting communications that are clear, accurate, and appropriate for sensitive topics.
- Comfortable working with engineering teams and technical decision-making; you can learn what makes technical work valuable and earn credibility in an engineer-led culture.
- Organized and detail-oriented with strong project management skills; you build systems to make sure nothing falls through the cracks, even when juggling multiple priorities.
- Able to operate as an extension of the CEO with real authority; when you tell someone something needs to happen, they know it carries the same weight as hearing it directly from the CEO.
- Low ego and high ownership mentality; no task is too small, you process feedback well, and you're trustworthy with confidential information.
- Familiarity with scaling frameworks like EOS (rhythm of business, accountability structures, systematic execution) is a major plus; experience with AI tools and automation for operational efficiency is also valuable.
Benefits:
- Competitive salary complemented by performance-based bonuses.
- Fully company-paid insurance packages, including health, dental, vision, disability, and life.
- A solid 401(k) plan with a 5% match of your base salary.
- 20 days of paid vacation with flexibility for more, adhering to jurisdictional regulations.
- 4 months of parental leave to cherish the arrival of new family members.
- $10,000 in relocation assistance to support your transition if interested in moving to NYC.
- $1,000 Working-from-Home stipend to create a comfortable and productive home office.
- Annual $750 Learning & Development stipend for continuous personal and professional growth.
- Company-sponsored all-team celebrations, including travel and accommodation, to foster community and recognize achievements.
- Philanthropic contribution matching up to $2,000 annually.
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